HCID 87222433、化合物 → HCID 87222515、化合物

HRID 712276ノート

反応式

HRID 712276 の反応式
C(O[K])(C)(C)C.[CH2:7]([NH:9][C:10]([NH:12][C:13]1[S:14][C:15]2[C:21](/[C:22](/[CH3:26])=[N:23]/[O:24][CH3:25])=[CH:20][C:19]([C:27]3[CH:28]=[N:29][C:30]([N:33]4[CH2:38][CH2:37][C:36]([CH3:44])([C:39]([O:41]CC)=[O:40])[CH2:35][CH2:34]4)=[N:31][CH:32]=3)=[CH:18][C:16]=2[N:17]=1)=[O:11])[CH3:8]>CS(C)=O>[CH2:7]([NH:9][C:10]([NH:12][C:13]1[S:14][C:15]2[C:21](/[C:22](/[CH3:26])=[N:23]/[O:24][CH3:25])=[CH:20][C:19]([C:27]3[CH:32]=[N:31][C:30]([N:33]4[CH2:38][CH2:37][C:36]([CH3:44])([C:39]([OH:41])=[O:40])[CH2:35][CH2:34]4)=[N:29][CH:28]=3)=[CH:18][C:16]=2[N:17]=1)=[O:11])[CH3:8]

参加物

4

反応物 2

HCID 87222433HCID 87222433、化合物HCID 178418922HCID 178418922、化合物

生成物 1

HCID 87222515HCID 87222515、化合物収率 40%

試薬・触媒・溶媒 1

HCID 679Dimethyl Sulfoxide溶媒

実験手順

tBuOK (124 mg, 1.11 mmol) was added to a solution of ethyl 1-[5-[2-(ethylcarbamoylamino)-7-[(E)-N-methoxy-C-methyl-carbonimidoyl]-1,3-benzothiazol-5-yl]pyrimidin-2-yl]-4-methyl-piperidine-4-carboxylate in DMSO (4 mL). The mixture was stirred at ambient temperature for 2 h after which time LCMS indicated clean conversion to the acid. The mixture was filtered through cotton wool to remove solid particulates and purified by preparative HPLC to give Compound 88 as a white solid, 76 mg, 40% yield over 2 steps. 1H NMR (DMSO-d6): δ 10.89 (1H, s), 8.85 (2H, s), 7.95 (1H, d, J=1.62 Hz), 7.76 (1H, d, J=1.69 Hz), 7.16 (1H, t, J=5.50 Hz), 4.32 (2H, dt, J=13.67, 4.40 Hz), 4.09 (3H, s), 3.38 (2H, ddd, J=13.49, 10.48, 3.40 Hz), 3.23 (2H, p, J=6.71 Hz), 2.42 (3H, s), 2.05 (2H, dt, J=13.34, 3.66 Hz), 1.41 (2H, ddd, J=13.34, 10.04, 3.92 Hz), 1.21 (3H, s), 1.14 (3H, t, J=7.15 Hz). MS: 512 [M+H]+.

後処理

  1. filtrationThe mixture was filtered through cotton wool
  2. customto remove solid particulates
  3. custompurified by preparative HPLC

出典と根拠

ORDレコード
ord-c049c60c51ae4d60aa26597ff75e326c
出典データセット
uspto-grants-2015_11
特許番号
US09181234B2

反応ノート

読み込み中…